Potassium Carbonate → 2-[4-(6-Chloro-2-pyridinyloxy)-phenoxymethyl]-5-bromothiophene

HRID 654436Notes

Reaction equation

[Cl:1][C:2]1[N:7]=[C:6]([O:8][C:9]2[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][CH:10]=2)[CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[Br:22][C:23]1[S:27][C:26]([CH2:28]Cl)=[CH:25][CH:24]=1>CN(C)C=O>[Cl:1][C:2]1[N:7]=[C:6]([O:8][C:9]2[CH:14]=[CH:13][C:12]([O:15][CH2:28][C:26]3[S:27][C:23]([Br:22])=[CH:24][CH:25]=3)=[CH:11][CH:10]=2)[CH:5]=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 20 °C

Procedure

3.5 g of 4-(6-chloro-2-pyridinyloxy)-phenol and 3.2 g of potassium carbonate are stirred for one hour at 60° C. in 100 ml of anhydrous dimethylformamide. Subsequently, 6.5 g of 5-bromo-2-chloromethylthiophene in 30 ml of anhydrous dimethylformamide is dripped in. The mixture is stirred for 6 hours at 80° C. and overnight at room temperature (about 20° C.). The mixture is then poured into 200 ml of ice water. The crude product which precipitates out is filtered off and recrystallized from n-hexane/ethyl acetate (4/1). There is obtained 3.1 g of 2-[4-(6-chloro-2-pyridinyloxy)-phenoxymethyl]-5-bromothiophene of m.p.: 78°-80° C.

Workup

customThe crude product which precipitates out
filtrationis filtered off
customrecrystallized from n-hexane/ethyl acetate (4/1)

Sources & evidence

ORD record: ord-d07f94d2748b48e9835a11a5b6b07939
Source dataset: uspto-grants-1992_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05132308

Reaction notes

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